Pleasant Valley Vacation Packages
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Your Pleasant Valley Vacation
The hassle-free way to experience this interesting city is with a tailor-made Pleasant Valley vacation package. Stay in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture or choose someplace else — our packages are all about you. If your trip to Pleasant Valley includes some sightseeing, visit renowned attractions like Marist College, Vassar College and Culinary Institute of America. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Pleasant Valley vacation is easy with Expedia.
Top Pleasant Valley Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Middletown - Goshen
Price was CA $1,098, price is now CA $874 per person
CA $874
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Newburgh (SWF)
8.6/10 Excellent! (1,002 reviews)
Easy check in, clean and smoke free, friendly staff, nice rooms, hot breakfast; would stay again!!!!
Reviewed on Jan 20, 2026
Microtel Inn & Suites by Wyndham Middletown
Price was CA $1,028, price is now CA $940 per person
CA $940
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Newburgh (SWF)
7/10 Good! (1,000 reviews)
The room was very clean. The staff was welcoming and polite. Not sure about The amenities was only there on a business trip. Overall would definitely stay again.
Reviewed on Dec 6, 2025
Howard Johnson by Wyndham Newburgh/West Point
Price was CA $692, price is now CA $633 per person
CA $633
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
6/10 (1,002 reviews)
The rooms are clean and well maintained with a fridge and microwave located inside the room. The staff were accommodating and welcoming.
Reviewed on Jan 24, 2026
Pleasant Valley Hotel Deals
Courtyard by Marriott Poughkeepsie
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Mar 2 to Mar 3
CA $144
CA $162 total
Mar 2 - Mar 3
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Very friendly, kind staff and clean room
Reviewed on Feb 2, 2026
Residence Inn by Marriott Kingston
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Mar 2 to Mar 3
CA $168
CA $188 total
Mar 2 - Mar 3
includes taxes & fees
8.8/10 Excellent! (833 reviews)
Have stayed here many times. they have done a really good job of keeping the property up to date. Very nice people.
Reviewed on Jan 25, 2026
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
25 OLD VINEYARD PLACE Hyde Park NY
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Feb 25 to Feb 26
CA $197
CA $223 total
Feb 25 - Feb 26
includes taxes & fees
9.6/10 Exceptional! (465 reviews)
The staff is incredibly courteous and helpful. The room is immaculate. Every amenity and convenience is considered in making your stay a pleasure.
Reviewed on Feb 1, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
